CA1145319A - Process for preparing unsaturated aliphatic esters from aliphatic dienes - Google Patents

Process for preparing unsaturated aliphatic esters from aliphatic dienes

Info

Publication number: CA1145319A
Authority: CA; Canada
Prior art keywords: palladium; aliphatic; group; conjugated diene; solvent
Prior art date: 1979-06-08
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA000351693A

Other languages

English (en)

French (fr)

Inventor

John F. Knifton

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Texaco Development Corp

Original Assignee

Texaco Development Corp

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1979-06-08

Filing date

1980-05-12

Publication date

1983-04-26

1980-05-12 Application filed by Texaco Development Corp filed Critical Texaco Development Corp

1983-04-26 Application granted granted Critical

1983-04-26 Publication of CA1145319A publication Critical patent/CA1145319A/en

Status Expired legal-status Critical Current

Links

-1 aliphatic dienes Chemical class 0.000 title claims abstract description 24
125000001931 aliphatic group Chemical group 0.000 title claims description 17
238000004519 manufacturing process Methods 0.000 title abstract description 4
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims abstract description 34
150000001993 dienes Chemical class 0.000 claims abstract description 34
239000002904 solvent Substances 0.000 claims abstract description 31
239000000758 substrate Substances 0.000 claims abstract description 22
150000002940 palladium Chemical class 0.000 claims abstract description 14
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 70
239000003054 catalyst Substances 0.000 claims description 34
229910052763 palladium Inorganic materials 0.000 claims description 31
150000002148 esters Chemical class 0.000 claims description 25
238000000034 method Methods 0.000 claims description 20
238000005810 carbonylation reaction Methods 0.000 claims description 17
239000003446 ligand Substances 0.000 claims description 16
YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 claims description 14
239000011541 reaction mixture Substances 0.000 claims description 14
230000015572 biosynthetic process Effects 0.000 claims description 11
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 10
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 10
125000004432 carbon atom Chemical group C* 0.000 claims description 9
229910002091 carbon monoxide Inorganic materials 0.000 claims description 9
GPNDARIEYHPYAY-UHFFFAOYSA-N palladium(ii) nitrate Chemical compound [Pd+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O GPNDARIEYHPYAY-UHFFFAOYSA-N 0.000 claims description 9
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
MUJIDPITZJWBSW-UHFFFAOYSA-N palladium(2+) Chemical compound [Pd+2] MUJIDPITZJWBSW-UHFFFAOYSA-N 0.000 claims description 8
239000000203 mixture Substances 0.000 claims description 7
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
229910052698 phosphorus Inorganic materials 0.000 claims description 6
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 5
230000003197 catalytic effect Effects 0.000 claims description 5
238000010438 heat treatment Methods 0.000 claims description 5
LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 claims description 5
JKDRQYIYVJVOPF-FDGPNNRMSA-L palladium(ii) acetylacetonate Chemical compound [Pd+2].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O JKDRQYIYVJVOPF-FDGPNNRMSA-L 0.000 claims description 5
239000011574 phosphorus Substances 0.000 claims description 5
FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical group C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 4
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 4
150000007933 aliphatic carboxylic acids Chemical class 0.000 claims description 4
RFLFDJSIZCCYIP-UHFFFAOYSA-L palladium(2+);sulfate Chemical compound [Pd+2].[O-]S([O-])(=O)=O RFLFDJSIZCCYIP-UHFFFAOYSA-L 0.000 claims description 4
PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 claims description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
JBYHSSAVUBIJMK-UHFFFAOYSA-N 1,4-oxathiane Chemical group C1CSCCO1 JBYHSSAVUBIJMK-UHFFFAOYSA-N 0.000 claims description 3
BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 claims description 3
WWZKQHOCKIZLMA-UHFFFAOYSA-M octanoate Chemical compound CCCCCCCC([O-])=O WWZKQHOCKIZLMA-UHFFFAOYSA-M 0.000 claims description 3
229910000364 palladium(II) sulfate Inorganic materials 0.000 claims description 3
WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 claims description 3
RMZAYIKUYWXQPB-UHFFFAOYSA-N trioctylphosphane Chemical compound CCCCCCCCP(CCCCCCCC)CCCCCCCC RMZAYIKUYWXQPB-UHFFFAOYSA-N 0.000 claims description 3
235000014113 dietary fatty acids Nutrition 0.000 claims description 2
230000000447 dimerizing effect Effects 0.000 claims description 2
239000000194 fatty acid Substances 0.000 claims description 2
229930195729 fatty acid Natural products 0.000 claims description 2
150000004665 fatty acids Chemical class 0.000 claims description 2
ZVSLRJWQDNRUDU-UHFFFAOYSA-L palladium(2+);propanoate Chemical compound [Pd+2].CCC([O-])=O.CCC([O-])=O ZVSLRJWQDNRUDU-UHFFFAOYSA-L 0.000 claims description 2
WXAZIUYTQHYBFW-UHFFFAOYSA-N tris(4-methylphenyl)phosphane Chemical compound C1=CC(C)=CC=C1P(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 WXAZIUYTQHYBFW-UHFFFAOYSA-N 0.000 claims description 2
239000003795 chemical substances by application Substances 0.000 claims 1
YUWBVKYVJWNVLE-UHFFFAOYSA-N [N].[P] Chemical compound [N].[P] YUWBVKYVJWNVLE-UHFFFAOYSA-N 0.000 abstract description 3
229940053200 antiepileptics fatty acid derivative Drugs 0.000 abstract 1
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 13
239000002253 acid Substances 0.000 description 12
230000006315 carbonylation Effects 0.000 description 12
238000006471 dimerization reaction Methods 0.000 description 12
125000000623 heterocyclic group Chemical group 0.000 description 10
150000007513 acids Chemical class 0.000 description 8
239000000047 product Substances 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 7
229910052757 nitrogen Inorganic materials 0.000 description 7
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 6
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
239000006227 byproduct Substances 0.000 description 6
239000001301 oxygen Substances 0.000 description 6
229910052760 oxygen Inorganic materials 0.000 description 6
238000003786 synthesis reaction Methods 0.000 description 5
RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 4
238000013019 agitation Methods 0.000 description 4
150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
230000035484 reaction time Effects 0.000 description 4
YWWDBCBWQNCYNR-UHFFFAOYSA-N trimethylphosphine Chemical compound CP(C)C YWWDBCBWQNCYNR-UHFFFAOYSA-N 0.000 description 4
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
239000005864 Sulphur Substances 0.000 description 3
230000000694 effects Effects 0.000 description 3
239000007789 gas Substances 0.000 description 3
230000004048 modification Effects 0.000 description 3
238000012986 modification Methods 0.000 description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
229920005862 polyol Polymers 0.000 description 3
150000003077 polyols Chemical class 0.000 description 3
PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 2
FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical compound C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
SDJHPPZKZZWAKF-UHFFFAOYSA-N 2,3-dimethylbuta-1,3-diene Chemical compound CC(=C)C(C)=C SDJHPPZKZZWAKF-UHFFFAOYSA-N 0.000 description 2
YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
238000005481 NMR spectroscopy Methods 0.000 description 2
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
125000004429 atom Chemical group 0.000 description 2
125000003262 carboxylic acid ester group Chemical group [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 description 2
150000001735 carboxylic acids Chemical class 0.000 description 2
239000012018 catalyst precursor Substances 0.000 description 2
YACLQRRMGMJLJV-UHFFFAOYSA-N chloroprene Chemical compound ClC(=C)C=C YACLQRRMGMJLJV-UHFFFAOYSA-N 0.000 description 2
238000001816 cooling Methods 0.000 description 2
TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 2
LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 2
239000012263 liquid product Substances 0.000 description 2
239000000314 lubricant Substances 0.000 description 2
SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 2
PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 2
150000004291 polyenes Chemical class 0.000 description 2
SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
MFKWGKFHTIWXRX-UHFFFAOYSA-N propan-2-yl nona-2,4-dienoate Chemical compound CCCCC=CC=CC(=O)OC(C)C MFKWGKFHTIWXRX-UHFFFAOYSA-N 0.000 description 2
VGAGMMQTYUWQOW-UHFFFAOYSA-N propan-2-yl nona-3,8-dienoate Chemical compound CC(C)OC(=O)CC=CCCCC=C VGAGMMQTYUWQOW-UHFFFAOYSA-N 0.000 description 2
229910052717 sulfur Inorganic materials 0.000 description 2
239000011593 sulfur Substances 0.000 description 2
TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 2
APPOKADJQUIAHP-GGWOSOGESA-N (2e,4e)-hexa-2,4-diene Chemical compound C\C=C\C=C\C APPOKADJQUIAHP-GGWOSOGESA-N 0.000 description 1
MYRHKQMPDBLATK-VOTSOKGWSA-N (3E)-nona-3,8-dienoic acid Chemical class OC(=O)C\C=C\CCCC=C MYRHKQMPDBLATK-VOTSOKGWSA-N 0.000 description 1
ZTJHDEXGCKAXRZ-FNORWQNLSA-N (3e)-octa-1,3,7-triene Chemical compound C=CCC\C=C\C=C ZTJHDEXGCKAXRZ-FNORWQNLSA-N 0.000 description 1
HOXGZVUCAYFWGR-UHFFFAOYSA-N 1,3,5-octatriene Chemical class CCC=CC=CC=C HOXGZVUCAYFWGR-UHFFFAOYSA-N 0.000 description 1
BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 description 1
FSSPGSAQUIYDCN-UHFFFAOYSA-N 1,3-Propane sultone Chemical compound O=S1(=O)CCCO1 FSSPGSAQUIYDCN-UHFFFAOYSA-N 0.000 description 1
VDFVNEFVBPFDSB-UHFFFAOYSA-N 1,3-dioxane Chemical compound C1COCOC1 VDFVNEFVBPFDSB-UHFFFAOYSA-N 0.000 description 1
WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 1
SDRZFSPCVYEJTP-UHFFFAOYSA-N 1-ethenylcyclohexene Chemical class C=CC1=CCCCC1 SDRZFSPCVYEJTP-UHFFFAOYSA-N 0.000 description 1
BBDKZWKEPDTENS-UHFFFAOYSA-N 4-Vinylcyclohexene Chemical compound C=CC1CCC=CC1 BBDKZWKEPDTENS-UHFFFAOYSA-N 0.000 description 1
MQWCXKGKQLNYQG-UHFFFAOYSA-N 4-methylcyclohexan-1-ol Chemical compound CC1CCC(O)CC1 MQWCXKGKQLNYQG-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 1
239000005956 Metaldehyde Substances 0.000 description 1
229910002666 PdCl2 Inorganic materials 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
239000000654 additive Substances 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
239000003513 alkali Substances 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
239000003708 ampul Substances 0.000 description 1
229910052787 antimony Inorganic materials 0.000 description 1
WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
229910052785 arsenic Inorganic materials 0.000 description 1
RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
VEZXCJBBBCKRPI-UHFFFAOYSA-N beta-propiolactone Chemical compound O=C1CCO1 VEZXCJBBBCKRPI-UHFFFAOYSA-N 0.000 description 1
VSGNNIFQASZAOI-UHFFFAOYSA-L calcium acetate Chemical compound [Ca+2].CC([O-])=O.CC([O-])=O VSGNNIFQASZAOI-UHFFFAOYSA-L 0.000 description 1
239000001639 calcium acetate Substances 0.000 description 1
235000011092 calcium acetate Nutrition 0.000 description 1
229960005147 calcium acetate Drugs 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
238000006555 catalytic reaction Methods 0.000 description 1
238000001311 chemical methods and process Methods 0.000 description 1
150000004292 cyclic ethers Chemical class 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
150000004294 cyclic thioethers Chemical class 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
230000002939 deleterious effect Effects 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 description 1
238000000921 elemental analysis Methods 0.000 description 1
238000009472 formulation Methods 0.000 description 1
150000002240 furans Chemical class 0.000 description 1
150000002391 heterocyclic compounds Chemical class 0.000 description 1
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
239000002815 homogeneous catalyst Substances 0.000 description 1
239000008240 homogeneous mixture Substances 0.000 description 1
BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical group [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
150000002596 lactones Chemical class 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
GKKDCARASOJPNG-UHFFFAOYSA-N metaldehyde Chemical compound CC1OC(C)OC(C)OC(C)O1 GKKDCARASOJPNG-UHFFFAOYSA-N 0.000 description 1
239000011707 mineral Substances 0.000 description 1
238000002156 mixing Methods 0.000 description 1
229910052754 neon Inorganic materials 0.000 description 1
GKAOGPIIYCISHV-UHFFFAOYSA-N neon atom Chemical compound [Ne] GKAOGPIIYCISHV-UHFFFAOYSA-N 0.000 description 1
238000006384 oligomerization reaction Methods 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
QJPQVXSHYBGQGM-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 QJPQVXSHYBGQGM-UHFFFAOYSA-N 0.000 description 1
UQPUONNXJVWHRM-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 UQPUONNXJVWHRM-UHFFFAOYSA-N 0.000 description 1
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
230000000737 periodic effect Effects 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
PTMHPRAIXMAOOB-UHFFFAOYSA-L phosphoramidate Chemical class NP([O-])([O-])=O PTMHPRAIXMAOOB-UHFFFAOYSA-L 0.000 description 1
238000000053 physical method Methods 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
229920000570 polyether Polymers 0.000 description 1
235000011056 potassium acetate Nutrition 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
239000001294 propane Substances 0.000 description 1
RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
238000010926 purge Methods 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000011084 recovery Methods 0.000 description 1
238000012552 review Methods 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
235000021003 saturated fats Nutrition 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
239000007787 solid Substances 0.000 description 1
241000894007 species Species 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000003107 substituted aryl group Chemical group 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
VOVUARRWDCVURC-UHFFFAOYSA-N thiirane Chemical compound C1CS1 VOVUARRWDCVURC-UHFFFAOYSA-N 0.000 description 1
229930192474 thiophene Natural products 0.000 description 1
150000003577 thiophenes Chemical class 0.000 description 1
UIUWNILCHFBLEQ-NSCUHMNNSA-N trans-pent-3-enoic acid Chemical compound C\C=C\CC(O)=O UIUWNILCHFBLEQ-NSCUHMNNSA-N 0.000 description 1
RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 0.000 description 1

Classifications

- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/22—Organic complexes
- B01J31/2204—Organic complexes the ligands containing oxygen or sulfur as complexing atoms
- B01J31/2208—Oxygen, e.g. acetylacetonates
- B01J31/2226—Anionic ligands, i.e. the overall ligand carries at least one formal negative charge
- B01J31/223—At least two oxygen atoms present in one at least bidentate or bridging ligand
- B01J31/2234—Beta-dicarbonyl ligands, e.g. acetylacetonates
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/22—Organic complexes
- B01J31/2204—Organic complexes the ligands containing oxygen or sulfur as complexing atoms
- B01J31/2208—Oxygen, e.g. acetylacetonates
- B01J31/2226—Anionic ligands, i.e. the overall ligand carries at least one formal negative charge
- B01J31/223—At least two oxygen atoms present in one at least bidentate or bridging ligand
- B01J31/2239—Bridging ligands, e.g. OAc in Cr2(OAc)4, Pt4(OAc)8 or dicarboxylate ligands
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/30—Addition reactions at carbon centres, i.e. to either C-C or C-X multiple bonds
- B01J2231/32—Addition reactions to C=C or C-C triple bonds
- B01J2231/321—Hydroformylation, metalformylation, carbonylation or hydroaminomethylation
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/82—Metals of the platinum group
- B01J2531/824—Palladium

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Chemical & Material Sciences (AREA)
Inorganic Chemistry (AREA)
Engineering & Computer Science (AREA)
Materials Engineering (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Catalysts (AREA)

CA000351693A 1979-06-08 1980-05-12 Process for preparing unsaturated aliphatic esters from aliphatic dienes Expired CA1145319A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US06/046,747 US4246183A (en)	1979-06-08	1979-06-08	Process for preparing unsaturated aliphatic esters from aliphatic dienes
US046,747		1979-06-08

Publications (1)

Publication Number	Publication Date
CA1145319A true CA1145319A (en)	1983-04-26

Family

ID=21945170

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000351693A Expired CA1145319A (en)	1979-06-08	1980-05-12	Process for preparing unsaturated aliphatic esters from aliphatic dienes

Country Status (11)

Country	Link
US (1)	US4246183A (da)
JP (1)	JPS55164648A (da)
BE (1)	BE883698A (da)
BR (1)	BR8003108A (da)
CA (1)	CA1145319A (da)
DE (1)	DE3019958A1 (da)
FR (1)	FR2458535A1 (da)
GB (1)	GB2052293B (da)
IT (1)	IT1150957B (da)
NL (1)	NL178864C (da)
ZA (1)	ZA803067B (da)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4269781A (en) *	1980-02-08	1981-05-26	Celanese Corporation	Dimeric carbonylation of 1,3-butadiene
GB2074040B (en) *	1980-04-22	1984-05-10	Air Prod & Chem	Catalysts for the synthesis of hydrogen peroxide
US4471067A (en) *	1981-11-09	1984-09-11	Celanese Corporation	Dimeric carbonylation of 1,3-alkadiene
US4416823A (en) *	1981-11-09	1983-11-22	Celanese Corporation	Dimeric carbonylation of 1,3-alkadiene
ATE78722T1 (de) *	1984-02-24	1992-08-15	Sagami Chem Res	Methode zum isomerisieren eines glycidats.
JPS60179147A (ja) *	1984-02-24	1985-09-13	Sagami Chem Res Center	異性化用触媒
KR930003649B1 (ko) *	1990-10-05	1993-05-08	재단법인 한국화학연구소	에틸리덴 디 아세테이트 제조용 고체촉매, 그의 제조방법 및 이를 이용한 연속식, 공정에 의한 에틸리덴 디 아세테이트의 제조방법
KR930003648B1 (ko) *	1990-10-05	1993-05-08	재단법인 한국화학연구소	에틸리덴 디 아세테이트 제조용 무기체 담지 촉매, 그 제조방법 및 이에 의한 에틸리덴 디 아세테이트의 제조방법
KR930003650B1 (ko) *	1990-10-08	1993-05-08	재단법인 한국화학연구소	에틸리덴 디 아세테이트 제조용 유기체 담지 촉매 및 이를 이용한 에틸리덴 디 아세테이트의 제조방법

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3670029A (en) *	1969-03-19	1972-06-13	Exxon Research Engineering Co	Preparation of unsaturated ethers
JPS50645A (da) *	1973-05-07	1975-01-07
US4124617A (en) *	1977-06-28	1978-11-07	Texaco Development Corporation	Process for preparing unsaturated aliphatic esters from aliphatic dienes
US4172087A (en) *	1978-02-13	1979-10-23	Texaco Development Corporation	Process for preparing unsaturated aliphatic esters from aliphatic dienes

1979
- 1979-06-08 US US06/046,747 patent/US4246183A/en not_active Expired - Lifetime
1980
- 1980-01-23 JP JP588680A patent/JPS55164648A/ja active Pending
- 1980-05-12 CA CA000351693A patent/CA1145319A/en not_active Expired
- 1980-05-19 BR BR8003108A patent/BR8003108A/pt unknown
- 1980-05-22 ZA ZA00803067A patent/ZA803067B/xx unknown
- 1980-05-24 DE DE19803019958 patent/DE3019958A1/de not_active Withdrawn
- 1980-06-03 NL NLAANVRAGE8003217,A patent/NL178864C/xx not_active IP Right Cessation
- 1980-06-06 BE BE0/200940A patent/BE883698A/fr not_active IP Right Cessation
- 1980-06-06 IT IT22649/80A patent/IT1150957B/it active
- 1980-06-06 FR FR8012598A patent/FR2458535A1/fr active Granted
- 1980-06-08 GB GB8016342A patent/GB2052293B/en not_active Expired

Also Published As

Publication number	Publication date
NL178864C (nl)	1986-06-02
ZA803067B (en)	1981-09-30
JPS55164648A (en)	1980-12-22
IT8022649A0 (it)	1980-06-06
NL178864B (nl)	1986-01-02
GB2052293A (en)	1981-01-28
NL8003217A (nl)	1980-12-10
IT1150957B (it)	1986-12-17
BE883698A (fr)	1980-10-01
FR2458535B1 (da)	1984-01-20
GB2052293B (en)	1983-04-27
US4246183A (en)	1981-01-20
DE3019958A1 (de)	1980-12-18
BR8003108A (pt)	1980-12-23
FR2458535A1 (fr)	1981-01-02

Legal Events

Date	Code	Title	Description
2000-04-26	MKEX	Expiry

Publication	Publication Date	Title
US4172087A (en)	1979-10-23	Process for preparing unsaturated aliphatic esters from aliphatic dienes
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CA1145319A (en)	1983-04-26	Process for preparing unsaturated aliphatic esters from aliphatic dienes
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US4895987A (en)	1990-01-23	Phosphonite-and phosphonite-promoted ruthenium - cobalt catalysts for the dealkoxyhydroxymethylation of acetals to form glycol ethers
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US4180694A (en)	1979-12-25	Production of 1,7-octadiene from butadiene
US3944604A (en)	1976-03-16	Production of propionic acid
EP0008139B1 (en)	1982-02-24	A process for preparing 1,7-octadiene
GB2024811A (en)	1980-01-16	Manufacturers of vicinal glycol esters from synthesis gas
EP0034374B1 (en)	1983-08-03	Selective homologation of acetals or ethers to monohydric or polyhydric alcohols
EP0312659A1 (en)	1989-04-26	Phosphonite-and phosphinite-promoted ruthenium - cobalt catalysts for the dealkoxyhydroxymethylation of acetals to form glycol ethers
US3892788A (en)	1975-07-01	Selective carboxylation process
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US4540810A (en)	1985-09-10	Manufacture of alkanol and glycol esters
KR950011108B1 (ko)	1995-09-28	β,γ-불포화산의 제조방법
US5304674A (en)	1994-04-19	Preparation of alkanedioic derivatives
US4529808A (en)	1985-07-16	Bi-solvent system for the hydroformylation of allyl alcohol using a rhodium catalyst
US4868328A (en)	1989-09-19	Selective oxidative carbonylation of conjugated dienes
US4461910A (en)	1984-07-24	Process for the co-production of dicarboxylates and acids
KR20000036150A (ko)	2000-06-26	ｎ-부틸알킬 에테르의 제조 방법
US3933884A (en)	1976-01-20	Process for preparing thiol esters